1. USA
  2. Florida
  3. Orlando
  4. Montego Bay
  5. Winter Rental

Montego Bay Winter Rentals & Holiday Homes

Discover winter rentals Montego Bay - We found 7382 exact matches

About Montego Bay Winter Rental on SunSkiResorts

Planning a winter vacation in Montego Bay? Discover 7382 places to stay, ideal for families, friends, groups, or wedding retreats.

At SunSkiResorts, explore a wide array of accommodations in Montego Bay, FL perfect for your seasonal escape. Our listings include private vacation homes, cabins, condos, villas, resorts, and pet-friendly apartments. SunSki's winter vacation homes feature top amenities such as Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.

Winter accommodations in Montego Bay start at US $389. The most popular properties in Montego Bay include cabins, bungalows, and rental homes. Planning a snowboarding adventure? Explore our snowboard-friendly ski resorts, chalets, and cabins available for short-term or long-term stays. Whether it's a weekend getaway, monthly retreat, or an extended stay, SunSki ensures a memorable winter trip.

To book your winter vacation homes in Montego Bay, visit SunSki's filter option, enter your travel dates, narrow down your preferences, and choose from our extensive list of rentals hassle-free. Explore our interactive map to uncover all accommodations in or around Montego Bay and unlock incredible deals.

Show more
Show less

Frequently Asked Questions About Montego Bay Winter Rentals

There are a lot of options in Montego Bay. If you plan on staying in the Montego Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in Montego Bay:

The average cost for winter rentals in Montego Bay is $389 per night. SunSki has a wide list of great winter places to stay near Montego Bay that would suit your preferences. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage/chalet rentals in Montego Bay that allow you to bring your pet or dog:

See all pet-friendly vacation rentals in Montego Bay on SunSkiResorts

Most of our rentals homes are suitable for families. Check out the complete list of places to stay in Montego Bay to find what works for you.
As of 2025, the data from SunSkiResorts shows that there are over 7382 private swimming pools or indoor pools accommodations near Montego Bay along with other great amenities.

About 7382 holiday rentals in Montego Bay boast of premium hot tubs. Some of the popular winter places to stay with hot tubs include:

Yes, there are many luxury places to stay in Montego Bay for the winter season. Find out more luxury, lakefront, winter, & last-minute rental homes near Montego Bay with all the best amenities for your next trip.